Trifluoroacetic acid → HCID 58641309, compound

Participants

Reaction Steps

To a flame-dried flask equipped with stir bar under nitrogen was charged 2-3 (0.71 g, 1.98 mmol) and anhydrous CH2Cl2 (50 mL). The resulting solution was treated with trifluoroacetic acid (10 mL) and stirred 1 hour at 25° C. Upon completion, the reaction was concentrated, taken up in CH2Cl2 (50 mL) and washed with 5% NaHCO3 (50 mL). The organic layer was dried (MgSO4), filtered and concentrated under reduced pressure. The resulting free-amine was dissolved in anhydrous CH2Cl2 (50 mL) and treated with p-nitrophenyl chloroformate (0.44 g, 2.17 mmol). The resulting solution was stirred 4 hours at 25° C. until completion. The reaction was concentrated to give 19-1 as a yellow oil: 1H NMR (300 MD, CDCl3) δ 8.22 (d, J=9.4 Hz, 1H), (d, J=9.1 Hz, 1H), 7.38 (m, 5H), 7.02 (m, 5H), 6.43 (m, 1H), 5.85 (m, 1H), 4.90 (m, 2H); LRMS m/z (M+H) 422.9 found, 423.1 required.

Provenance & Evidence